Front Cover: Asymmetric Synthesis of 3‐Pyrrolines through an Aryne‐Induced Domino Process (Asian J. Org. Chem. 4/2021). Issue 4 (9th April 2021)

• Record Type: Journal Article
• Authors: Hwu, Jih Ru; Panja, Avijit; Gupta, Nitesh K.; Huang, Wen‐Chieh; Hu, Yu‐Chen; Lin, Chun‐Cheng; Hwang, Kuo‐Chu; Chan, Wei‐Jen; Tsay, Shwu‐Chen
• Is Part Of: Asian journal of organic chemistry. Volume 10:Issue 4(2021)
• Page Start: 679
• Page End: 679
• Publication Date: 2021-04-09
• Subjects: domino -- aryne -- 1, 3-dipolar cycloaddition -- asymmetric synthesis -- pyrroline; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202100140
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract : A new domino reaction is developed for the synthesis of optically active 3‐pyrrolines. The reaction involves the use of (trimethylsilyl)aryl triflates, KF, Schiff bases, and alkynes in the presence of a chiral catalyst (R)‐(–)‐1, 1′‐binaphthyl‐2, 2′‐diyl hydrogenphosphate. The key features of this reaction include the generation of a single product in very good yields with high stereo‐ and enantioselectivity. The enantiomeric ratio reaches as high as 98.5:1.5. The overall pathway includes four steps in a domino process of 1, 2‐elimination, 1, 2‐nucleophilic addition, 1, 4‐proton shift, and (3+2) cycloaddition. More information can be found in the Full Paper by Jih Ru Hwu et al.